Conformationally Selective Synthesis of Mononitrocalix[4]arene in Cone or Partial Cone. Issue 5 (10th May 2017)

• Record Type: Journal Article
• Authors: Royappa, Ana Rita N. S.; Ayer, Maxime; Fracassi, Alessandro; Ebert, Marc‐Olivier; Aroua, Safwan; Yamakoshi, Yoko
• Is Part Of: Helvetica chimica acta. Volume 100:Issue 5(2017)
• Page Start: n/a
• Page End: n/a
• Publication Date: 2017-05-10
• Subjects: Nitrocalixarenes -- Cone conformation -- Partial cone conformation -- NMR -- Flexible container; Chemistry -- Periodicals; Chemistry, Analytical -- periodicals; Chimie -- Périodiques; 540
• DOI: 10.1002/hlca.201600391
• Languages: English
• ISSNs: 0018-019X

Abstract

Abstract : Nitro‐substituted calixarenes in a cone and a partial cone conformation were prepared selectively using distinct synthetic routes. The selective nitration of tris‐ or penta‐substituted phenols of calix[4]arene or calix[6]arene provided mononitrocalix[ n ]arenes ( n = 4, 6). Subsequent addition of ethylene glycol (EG) moieties to mononitrocalix[4]arene provided tetraEGylcalix[4]arene in locked partial cone conformation. By an alternative route – initial addition of EG moieties to the non‐derivatized calix[4]arene followed by the uncontrolled nitration – provided mononitro‐ and dinitro‐tetraEGylcalix[4]arenes locked in the cone conformation. These nitrocalix[4]arenes with locked cone or partial cone conformation are useful building blocks for further assembly of supramolecular systems, especially in the area of material sciences. Abstract :